Potassium Carbonate → HCID 86729612, compound

HRID 2277745Notes

Reaction equation

HRID 2277745 reaction equation
[Cl:1][C:2]1[N:7]=[C:6](Cl)[C:5]([F:9])=[CH:4][N:3]=1.[O:10]1[C:19]2[C:14](=[CH:15][CH:16]=[CH:17][C:18]=2B(O)O)[CH2:13][CH2:12][CH2:11]1.C(=O)([O-])[O-].[K+].[K+]>COCCOC.C(OCC)(=O)C.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.Cl[Pd]Cl>[Cl:1][C:2]1[N:7]=[C:6]([C:18]2[CH:17]=[CH:16][CH:15]=[C:14]3[C:19]=2[O:10][CH2:11][CH2:12][CH2:13]3)[C:5]([F:9])=[CH:4][N:3]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2507052,4-Dichloro-5-fluoropyrimidineHCID 534384643,4-Dihydro-2H-1-benzopyran-8-ylboronic acid

Product 1

HCID 86729612HCID 86729612, compoundYield 78.4%

Reagents, catalysts & solvents 3

HCID 6102075Dichlorobis(triphenylphosphine)palladiumCatalystHCID 80711,2-DimethoxyethaneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A batch with 2,4-dichloro-5-fluoropyrimidine (565 mg; 3.28 mmol; Aldrich Chemical Company Inc.), 3,4-dihydro-2H-chromen-8-ylboronic acid (643 mg; 3.61 mmol; Parkway Scientific LLC) and bis(triphenylphosphine)palladium(II)chloride (230 mg; 0.33 mmol; Aldrich Chemical Company Inc.) in 1,2-dimethoxyethane (5.4 ml) and 2M solution of potassium carbonate (4.9 ml) was degassed using argon. The batch was stirred under argon for 16 hours at 90° C. After cooling the batch was diluted with ethyl acetate and washed with saturated aqueous sodium chloride solution. The organic phase was dried (sodium sulfate), filtered and concentrated. The residue was purified by chromatography (hexane/ethyl acetate 2%-20%) to give the desired product (701 mg; 2.57 mmol).

Workup

  1. temperatureAfter cooling the batch
  2. washwashed with saturated aqueous sodium chloride solution
  3. dry with materialThe organic phase was dried (sodium sulfate)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe residue was purified by chromatography (hexane/ethyl acetate 2%-20%)

Sources & evidence

ORD record
ord-dd35cd4cd8394b1cb235c470014bd3eb
Source dataset
uspto-grants-2015_09
Patent number
US09133171B2

Reaction notes

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